EP2531035B1 - Synergistic herbicidal composition containing penoxsulam and flazasulfuron - Google Patents
Synergistic herbicidal composition containing penoxsulam and flazasulfuron Download PDFInfo
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- EP2531035B1 EP2531035B1 EP11702771.4A EP11702771A EP2531035B1 EP 2531035 B1 EP2531035 B1 EP 2531035B1 EP 11702771 A EP11702771 A EP 11702771A EP 2531035 B1 EP2531035 B1 EP 2531035B1
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- Prior art keywords
- gai
- flazasulfuron
- penoxsulam
- herbicidal mixture
- synergistic herbicidal
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
Definitions
- herbicidal active ingredients have been shown to be more effective in combination than when applied individually and this is referred to as "synergism.”
- ⁇ synergism' [is] an interaction of two or more factors such that the effect when combined is greater than the predicted effect based on the response to each factor applied separately.
- the present invention is based on the discovery that flazasulfuron and penoxsulam, already known individually for their herbicidal efficacy, display a synergistic effect when applied in combination.
- herbicidal compounds forming the synergistic composition of this invention are independently known in the art for their effects on plant growth.
- EP 2 052 606 A1 describes herbicidal compositions which, among others, may comprise penoxsulam.
- WO 2004/080171 A2 describes herbicidal mixtures which, amoung others, may comprise flazasulfuron.
- the present invention concerns a synergistic herbicidal mixture comprising an herbicidally effective amount of (a) penoxsulam and (b) flazasulfuron.
- the compositions may also contain an agriculturally acceptable adjuvant or carrier.
- the present invention also concerns a method of controlling the growth of undesirable vegetation, particularly in fruit trees, including pome, stone, tree nut, citrus and olives, in grapevines, in turf, in sugar cane, in parks and alleyways, in range and pasture and in industrial vegetation management.
- Penoxsulam is the common name for (2-(2,2-difluoroethoxy)- N -(5,8- dimethoxy-[1,2,4]triazola[1,5-c]pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006 . Penoxsulam controls barnyard grass, as well as many broad-leaved, sedge and aquatic weeds in rice.
- Flazasulfuron is the common name for 1-(4,6-dimethoxypyrimidin-2-yl)-3-(3-trifluoromethyl-2-pyridylsulfonyl)urea. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006 . Flazasulfuron controls grasses, broad-leaved weeds and sedges.
- herbicide is used herein to mean an active ingredient that kills, controls or otherwise adversely modifies the growth of plants.
- An herbicidally effective or vegetation controlling amount is an amount of active ingredient which causes an adversely modifying effect and includes deviations from natural development, killing, regulation, desiccation, retardation, and the like.
- plants and vegetation include germinant seeds, emerging seedlings and established vegetation.
- Herbicidal activity is exhibited by the compounds of the synergistic mixture when they are applied directly to the plant or to the locus of the plant at any stage of growth or before planting or emergence. The effect observed depends upon the plant species to be controlled, the stage of growth of the plant, the application parameters of dilution and spray drop size, the particle size of solid components, the environmental conditions at the time of use, the specific compound employed, the specific adjuvants and carriers employed, the soil type, and the like, as well as the amount of chemical applied. These and other factors can be adjusted as is known in the art to promote non-selective or selective herbicidal action. Generally, it is preferred to apply the composition of the present invention postemergence to relatively immature undesirable vegetation to achieve the maximum control of weeds.
- the active ingredient ratio (wt:wt) of Flazasulfuron to penoxsulam at which the herbicidal effect is synergistic lies within the range of between 1:2.5 and 15:1 with a ratio of 3.5:1 being preferred.
- the rate at which the synergistic composition is applied will depend upon the particular type of weed to be controlled, the degree of control required, and the timing and method of application.
- the composition of the invention can be applied at an application rate of between 14 grams active ingredient per hectare (gai/ha) and 200 gai/ha based on the total amount of active ingredients in the composition.
- An application rate between 20 gai/ha and 150 gai/ha is preferred.
- flazasulfuron is applied at a rate between 15 gai/ha and 100 gai/ha
- penoxsulam is applied at a rate between 5 gai/ha and 50 gai/ha.
- the components of the synergistic mixture of the present invention can be applied either separately or as part of a multipart herbicidal system.
- the synergistic mixture of the present invention can be applied in conjunction with one or more other herbicides to control a wider variety of undesirable vegetation.
- the composition can be formulated with the other herbicide or herbicides, tank mixed with the other herbicide or herbicides or applied sequentially with the other herbicide or herbicides.
- the synergistic mixture of the present invention can be used on acetolactate synthase inhibitor tolerant crops.
- the synergistic composition of the present invention can further be used in conjunction with 2,4-D, glyphosate, glufosinate, dicamba or imidazolinones on 2,4-D tolerant, glyphosate-tolerant, glufosinate-tolerant, dicamba-tolerant or imidazolinone-tolerant crops.
- synergistic composition of the present invention in combination with herbicides that are selective for the crop being treated and which complement the spectrum of weeds controlled by these compounds at the application rate employed. It is further generally preferred to apply the synergistic composition of the present invention and other complementary herbicides at the same time, either as a combination formulation or as a tank mix.
- the synergistic composition of the present invention can generally be employed in combination with known herbicide safeners, such as benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl), cyometrinil, cyprosulfamate, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephanate, MG 191, MON 4660, naphthalic anhydride (NA), oxabetrinil, R29148 and N-phenyl-sulfonylbenzoic acid amides, to enhance their selectivity.
- herbicide safeners such as benoxacor, benthiocarb, brassinolide, cloquintocet (
- the synergistic composition of the present invention in mixtures containing an herbicidally effective amount of the herbicidal components along with at least one agriculturally acceptable adjuvant or carrier.
- Suitable adjuvants or carriers should not be phytotoxic to valuable crops, particularly at the concentrations employed in applying the compositions for selective weed control in the presence of crops, and should not react chemically with herbicidal components or other composition ingredients.
- Such mixtures can be designed for application directly to weeds or their locus or can be concentrates or formulations that are normally diluted with additional carriers and adjuvants before application.
- They can be solids, such as, for example, dusts, granules, water dispersible granules, or wettable powders, or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions.
- Suitable agricultural adjuvants and carriers that are useful in preparing the herbicidal mixtures of the invention are well known to those skilled in the art.
- Some of these adjuvants include, but are not limited to, crop oil concentrate (mineral oil (85%) + emulsifiers (15%)); nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C 9 -C 1 alkylpolyglycoside; phosphated alcohol ethoxylate; natural primary alcohol (C 12 -C 16 ) ethoxylate; di-sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow
- Liquid carriers that can be employed include water and organic solvents.
- the organic solvents typically used include, but are not limited to, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cotton seed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; esters of monoalcohols or dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters of mono, di and polycar
- organic solvents include toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerine, N -methyl-2-pyrrolidinone, N,N- dimethyl alkylamides, dimethyl sulfoxide, liquid fertilizers and the like. Water is generally the carrier of choice for the dilution of concentrates.
- Suitable solid carriers include talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, and the like.
- compositions of the present invention are advantageously employed in both solid and liquid compositions, especially those designed to be diluted with carrier before application.
- the surface-active agents can be anionic, cationic or nonionic in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes.
- Surfactants conventionally used in the art of formulation and which may also be used in the present formulations are described, inter alia, in “ McCutcheon's Detergents and Emulsifiers Annual," MC Publishing Corp., Ridgewood, New Jersey, 1998 and in “ Encyclopedia of Surfactants,” Vol. I-III, Chemical Publishing Co., New York, 1980 -81.
- Typical surface-active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C 18 ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C 16 ethoxylate; soaps, such as sodium stearate; alkylnaphthalene-sulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty
- compositions may also contain other compatible components, for example, other herbicides, plant growth regulants, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like.
- the concentration of the active ingredients in the synergistic composition of the present invention is generally from 0.001 to 98 percent by weight. Concentrations from 0.01 to 90 percent by weight are often employed. In compositions designed to be employed as concentrates, the active ingredients are generally present in a concentration from 5 to 98 weight percent, preferably 10 to 90 weight percent. Such compositions are typically diluted with an inert carrier, such as water, before application. The diluted compositions usually applied to weeds or the locus of weeds generally contain 0.0001 to 1 weight percent active ingredient and preferably contain 0.001 to 0.05 weight percent.
- compositions can be applied to weeds or their locus by the use of conventional ground or aerial dusters, sprayers, and granule applicators, by addition to irrigation water, and by other conventional means known to those skilled in the art.
- Trial sites were located in commercially grown vines of European grape (Vitis vinifera). The grapes were grown using normal cultural practices for fertilization, seeding, and maintenance to ensure good growth of the crop and the weeds. The trials were conducted using normal research methodology. Trial plots were between 2 to 4.5 meters (m) wide by 5.5 to 10 m long. All treatments were applied using a randomized complete block trial design with 3 or 4 replications per treatment. The trial sites had naturally occurring populations of weeds.
- the weed spectrum included, but was not limited to, black nightshade (Solanum nigrum, SOLNI), pigeongrass or foxtail millet (Setaria sp., SETSS), common lambsquarter ( Chenopodium album, CHEAL), round-leaved cranesbill ( Geranium rotundifolium, GERRT), common groundsel ( Senecio vulgaris, SENVU), mallow ( Malva L., MALSS) and common purslane ( Portulaca oleracea, POROL).
- Treatments consisted of tank mixes of an oil dispersion of penoxsulam and commercially available formulations of flazasulfuron (Katana herbicide, water dispersible granules) applied in water.
- the application volumes were between 150-325 liters per hectare (L/ha). All application were made using precision gas hand sprayers using a 2 or 3 m boom using flat fan (80° or 110 °) nozzles to broadcast the treatments on the soil.
- the treated plots and control plots were rated blind at various intervals after application. Ratings were based of Percent (%) Visual weed control, where 0 corresponds to no injury and 100 corresponds to complete kill.
- Colby's equation was used to determine the herbicidal effects expected from the mixtures ( Colby, S. R. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 1967 15, 20-22 ).
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Description
- The protection of crops from weeds and other vegetation which inhibit crop growth is a constantly recurring problem in agriculture. To help combat this problem, researchers in the field of synthetic chemistry have produced an extensive variety of chemicals and chemical formulations effective in the control of such unwanted growth. Chemical herbicides of many types have been disclosed in the literature and a large number are in commercial use.
- In some cases, herbicidal active ingredients have been shown to be more effective in combination than when applied individually and this is referred to as "synergism." As described in the Herbicide Handbook of the Weed Science Society of America, Eighth Edition, 2002, p. 462, "`synergism' [is] an interaction of two or more factors such that the effect when combined is greater than the predicted effect based on the response to each factor applied separately." The present invention is based on the discovery that flazasulfuron and penoxsulam, already known individually for their herbicidal efficacy, display a synergistic effect when applied in combination.
- The herbicidal compounds forming the synergistic composition of this invention are independently known in the art for their effects on plant growth. For instance,
EP 2 052 606 A1 describes herbicidal compositions which, among others, may comprise penoxsulam.WO 2004/080171 A2 describes herbicidal mixtures which, amoung others, may comprise flazasulfuron. - The present invention concerns a synergistic herbicidal mixture comprising an herbicidally effective amount of (a) penoxsulam and (b) flazasulfuron. The compositions may also contain an agriculturally acceptable adjuvant or carrier.
- The present invention also concerns a method of controlling the growth of undesirable vegetation, particularly in fruit trees, including pome, stone, tree nut, citrus and olives, in grapevines, in turf, in sugar cane, in parks and alleyways, in range and pasture and in industrial vegetation management.
- Penoxsulam is the common name for (2-(2,2-difluoroethoxy)-N-(5,8- dimethoxy-[1,2,4]triazola[1,5-c]pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Penoxsulam controls barnyard grass, as well as many broad-leaved, sedge and aquatic weeds in rice.
- Flazasulfuron is the common name for 1-(4,6-dimethoxypyrimidin-2-yl)-3-(3-trifluoromethyl-2-pyridylsulfonyl)urea. Its herbicidal activity is described in The Pesticide Manual, Fourteenth Edition, 2006. Flazasulfuron controls grasses, broad-leaved weeds and sedges.
- The term herbicide is used herein to mean an active ingredient that kills, controls or otherwise adversely modifies the growth of plants. An herbicidally effective or vegetation controlling amount is an amount of active ingredient which causes an adversely modifying effect and includes deviations from natural development, killing, regulation, desiccation, retardation, and the like. The terms plants and vegetation include germinant seeds, emerging seedlings and established vegetation.
- Herbicidal activity is exhibited by the compounds of the synergistic mixture when they are applied directly to the plant or to the locus of the plant at any stage of growth or before planting or emergence. The effect observed depends upon the plant species to be controlled, the stage of growth of the plant, the application parameters of dilution and spray drop size, the particle size of solid components, the environmental conditions at the time of use, the specific compound employed, the specific adjuvants and carriers employed, the soil type, and the like, as well as the amount of chemical applied. These and other factors can be adjusted as is known in the art to promote non-selective or selective herbicidal action. Generally, it is preferred to apply the composition of the present invention postemergence to relatively immature undesirable vegetation to achieve the maximum control of weeds.
- In the composition of this invention, the active ingredient ratio (wt:wt) of Flazasulfuron to penoxsulam at which the herbicidal effect is synergistic lies within the range of between 1:2.5 and 15:1 with a ratio of 3.5:1 being preferred.
- The rate at which the synergistic composition is applied will depend upon the particular type of weed to be controlled, the degree of control required, and the timing and method of application. In general, the composition of the invention can be applied at an application rate of between 14 grams active ingredient per hectare (gai/ha) and 200 gai/ha based on the total amount of active ingredients in the composition. An application rate between 20 gai/ha and 150 gai/ha is preferred. In an especially preferred embodiment of the invention, flazasulfuron is applied at a rate between 15 gai/ha and 100 gai/ha, and penoxsulam is applied at a rate between 5 gai/ha and 50 gai/ha.
- The components of the synergistic mixture of the present invention can be applied either separately or as part of a multipart herbicidal system.
- The synergistic mixture of the present invention can be applied in conjunction with one or more other herbicides to control a wider variety of undesirable vegetation. When used in conjunction with other herbicides, the composition can be formulated with the other herbicide or herbicides, tank mixed with the other herbicide or herbicides or applied sequentially with the other herbicide or herbicides. Some of the herbicides that can be employed in conjunction with the synergistic composition of the present invention include: 4-CPA; 4-CPB; 4-CPP; 2,4-D; 3,4-DA; 2,4-DB; 3,4-DB; 2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB; acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amiprofos-methyl, amitrole, ammonium sulfamate, anilofos, anisuron, asulam, atraton, atrazine, azafenidin, azimsulfuron, aziprotryne, barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin, benfuresate, bensulfuron, bensulide, bentazone, benzadox, benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor, benzoylprop, benzthiazuron, bicyclopyrone, bifenox, bilanafos, bispyribac, borax, bromacil, bromobonil, bromobutide, bromofenoxim, bromoxynil, brompyrazon, butachlor, butafenacil, butamifos, butenachlor, buthidazole, buthiuron, butralin, butroxydim, buturon, butylate, cacodylic acid, cafenstrole, calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole chlorprocarb, carfentrazone, CDEA, CEPC, chlomethoxyfen, chloramben, chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlornitrofen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, cisanilide, clethodim, cliodinate, clodinafop, clofop, clomazone, clomeprop, cloprop, cloproxydim, clopyralid, cloransulam, CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumyluron, cyanatryn, cyanazine, cycloate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop, cyperquat, cyprazine, cyprazole, cypromid, daimuron, dalapon, dazomet, delachlor, desmedipham, desmetryn, di-allate, dicamba, dichlobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop-P, diclofop, diclosulam, diethamquat, diethatyl, difenopenten, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimexano, dimidazon, dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, disul, dithiopyr, diuron, DMPA, DNOC, DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, erbon, esprocarb, ethalfluralin, ethametsulfuron, ethidimuron, ethiolate, ethofumesate, ethoxyfen, ethoxysulfuron, etinofen, etnipromid, etobenzanid, EXD, fenasulam, fenoprop, fenoxaprop, fenoxaprop-P, fenoxasulfone, fenteracol, fenthiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flamprop-M, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenican, flufenpyr, flumetsulam, flumezin, flumiclorac, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron, flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fomesafen, foramsulfuron, fosamine, furyloxyfen, glufosinate, glufosinate-P, glyphosate, halosafen, halosulfuron, haloxydine, haloxyfop, haloxyfop-P, hexachloroacetone, hexaflurate, hexazinone, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, indanofan, indaziflam, iodobonil, iodomethane, iodosulfuron, ioxynil, ipazine, ipfencarbazone, iprymidam, isocarbamid, isocil, isomethiozin, isonoruron, isopolinate, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, ketospiradox, lactofen, lenacil, linuron, MAA, MAMA, MCPA, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamifop, metamitron, metazachlor, metazosulfuron, metflurazon, methabenzthiazuron, methalpropalin, methazole, methiobencarb, methiozolin, methiuron, methometon, methoprotryne, methyl bromide, methyl isothiocyanate, methyldymron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide, naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noruron, OCH, orbencarb, ortho-dichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone, oxyfluorfen, parafluron, paraquat, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, phenobenzuron, phenylmercury acetate, picloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron, procyazine, prodiamine, profluazol, profluralin, profoxydim, proglinazine, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfalin, prosulfocarb, prosulfuron, proxan, prynachlor, pydanon, pyraclonil, pyraflufen, pyrasulfotole, pyrazolynate, pyrazosulfuron, pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor, pyridafol, pyridate, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quinonamid, quizalofop, quizalofop-P, rhodethanil, rimsulfuron, saflufenacil, S-metolachlor, sebuthylazine, secbumeton, sethoxydim, siduron, simazine, simeton, simetryn, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone, sulfometuron, sulfosulfuron, sulfuric acid, sulglycapin, swep, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn, tetrafluron, thenylchlor, thiazafluron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone-methyl, thifensulfuron, thiobencarb, tiocarbazil, tioclorim, topramezone, tralkoxydim, tri-allate, triasulfuron, triaziflam, tribenuron, tricamba, triclopyr, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac tritosulfuron, vernolate and xylachlor.
- The synergistic mixture of the present invention can be used on acetolactate synthase inhibitor tolerant crops. The synergistic composition of the present invention can further be used in conjunction with 2,4-D, glyphosate, glufosinate, dicamba or imidazolinones on 2,4-D tolerant, glyphosate-tolerant, glufosinate-tolerant, dicamba-tolerant or imidazolinone-tolerant crops.
- It is generally preferred to use the synergistic composition of the present invention in combination with herbicides that are selective for the crop being treated and which complement the spectrum of weeds controlled by these compounds at the application rate employed. It is further generally preferred to apply the synergistic composition of the present invention and other complementary herbicides at the same time, either as a combination formulation or as a tank mix.
- The synergistic composition of the present invention can generally be employed in combination with known herbicide safeners, such as benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl), cyometrinil, cyprosulfamate, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephanate, MG 191, MON 4660, naphthalic anhydride (NA), oxabetrinil, R29148 and N-phenyl-sulfonylbenzoic acid amides, to enhance their selectivity.
- In practice, it is preferable to use the synergistic composition of the present invention in mixtures containing an herbicidally effective amount of the herbicidal components along with at least one agriculturally acceptable adjuvant or carrier. Suitable adjuvants or carriers should not be phytotoxic to valuable crops, particularly at the concentrations employed in applying the compositions for selective weed control in the presence of crops, and should not react chemically with herbicidal components or other composition ingredients. Such mixtures can be designed for application directly to weeds or their locus or can be concentrates or formulations that are normally diluted with additional carriers and adjuvants before application. They can be solids, such as, for example, dusts, granules, water dispersible granules, or wettable powders, or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions.
- Suitable agricultural adjuvants and carriers that are useful in preparing the herbicidal mixtures of the invention are well known to those skilled in the art. Some of these adjuvants include, but are not limited to, crop oil concentrate (mineral oil (85%) + emulsifiers (15%)); nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C9-C1 alkylpolyglycoside; phosphated alcohol ethoxylate; natural primary alcohol (C12-C16) ethoxylate; di-sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15 EO); PEG(400) dioleate-99.
- Liquid carriers that can be employed include water and organic solvents. The organic solvents typically used include, but are not limited to, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cotton seed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; esters of monoalcohols or dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters of mono, di and polycarboxylic acids and the like. Specific organic solvents include toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerine, N-methyl-2-pyrrolidinone, N,N-dimethyl alkylamides, dimethyl sulfoxide, liquid fertilizers and the like. Water is generally the carrier of choice for the dilution of concentrates.
- Suitable solid carriers include talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, and the like.
- It is usually desirable to incorporate one or more surface-active agents into the compositions of the present invention. Such surface-active agents are advantageously employed in both solid and liquid compositions, especially those designed to be diluted with carrier before application. The surface-active agents can be anionic, cationic or nonionic in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes. Surfactants conventionally used in the art of formulation and which may also be used in the present formulations are described, inter alia, in "McCutcheon's Detergents and Emulsifiers Annual," MC Publishing Corp., Ridgewood, New Jersey, 1998 and in "Encyclopedia of Surfactants," Vol. I-III, Chemical Publishing Co., New York, 1980-81. Typical surface-active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C18 ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C16 ethoxylate; soaps, such as sodium stearate; alkylnaphthalene-sulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; salts of mono- and dialkyl phosphate esters; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cotton seed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; and esters of the above vegetable oils.
- Other adjuvants commonly used in agricultural compositions include compatibilizing agents, antifoam agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, sticking agents, dispersing agents, thickening agents, freezing point depressants, antimicrobial agents, and the like. The compositions may also contain other compatible components, for example, other herbicides, plant growth regulants, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like.
- The concentration of the active ingredients in the synergistic composition of the present invention is generally from 0.001 to 98 percent by weight. Concentrations from 0.01 to 90 percent by weight are often employed. In compositions designed to be employed as concentrates, the active ingredients are generally present in a concentration from 5 to 98 weight percent, preferably 10 to 90 weight percent. Such compositions are typically diluted with an inert carrier, such as water, before application. The diluted compositions usually applied to weeds or the locus of weeds generally contain 0.0001 to 1 weight percent active ingredient and preferably contain 0.001 to 0.05 weight percent.
- The present compositions can be applied to weeds or their locus by the use of conventional ground or aerial dusters, sprayers, and granule applicators, by addition to irrigation water, and by other conventional means known to those skilled in the art.
- The following examples illustrate the present invention.
- These trials were conducted under field conditions in France. Trial sites were located in commercially grown vines of European grape (Vitis vinifera). The grapes were grown using normal cultural practices for fertilization, seeding, and maintenance to ensure good growth of the crop and the weeds. The trials were conducted using normal research methodology. Trial plots were between 2 to 4.5 meters (m) wide by 5.5 to 10 m long. All treatments were applied using a randomized complete block trial design with 3 or 4 replications per treatment. The trial sites had naturally occurring populations of weeds. The weed spectrum included, but was not limited to, black nightshade (Solanum nigrum, SOLNI), pigeongrass or foxtail millet (Setaria sp., SETSS), common lambsquarter (Chenopodium album, CHEAL), round-leaved cranesbill (Geranium rotundifolium, GERRT), common groundsel (Senecio vulgaris, SENVU), mallow (Malva L., MALSS) and common purslane (Portulaca oleracea, POROL).
- Treatments consisted of tank mixes of an oil dispersion of penoxsulam and commercially available formulations of flazasulfuron (Katana herbicide, water dispersible granules) applied in water. The application volumes were between 150-325 liters per hectare (L/ha). All application were made using precision gas hand sprayers using a 2 or 3 m boom using flat fan (80° or 110 °) nozzles to broadcast the treatments on the soil.
- The treated plots and control plots were rated blind at various intervals after application. Ratings were based of Percent (%) Visual weed control, where 0 corresponds to no injury and 100 corresponds to complete kill.
- Data was collected for all trials and analyzed using various statistical methods.
- Colby's equation was used to determine the herbicidal effects expected from the mixtures (Colby, S. R. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 1967 15, 20-22).
-
- A = observed efficacy of active ingredient A at the same concentration as used in the mixture;
- B = observed efficacy of active ingredient B at the same concentration as used in the mixture.
- The results are summarized in Tables 1 through 3.
Table 1. Synergistic weed control following an application of Penoxsulam + Flazasulfuron 68 to 147 days after application - Field trial #1. Penoxsulam Flazasulfuron SOLNI (1) SOLNI (2) SETSS CHEAL (rate in grams ai/ha) Obs Expected* Obs Expected* Obs Expected* Obs Expected* 7 0 1 - 17 - 1 - 0 - 0 25 6 - 58 - 73 - 63 - 7 25 36 7 94 65 83 73 80 63 SOLNI - black nightshade (Solanum nigrum)
SETSS - pigeongrass or foxtail millet (Setaria sp.)
CHEAL - common lambsquarter (Chenopodium album)
grams ai/ha - grams of active ingredient per hectare
Obs - percent control observed
Expected* - percent control expected by Colby equation
(1) = Port A Binson, France
(2) = Echallat, FranceTable 2. Synergistic weed control following an application of Penoxsulam + Flazasulfuron 118 to 158 days after application - Field trial #2. Penoxsulam Flazasulfuron GERRT SENVU MALSS POROL (rate in grams ai/ha) Obs Expected* Obs Expected* Obs Expected* Obs Expected* 7 0 13 - 3 - 20 - 0 0 25 23 - 30 - 53 - 78 - 7 25 73 33 73 32 77 62 99 78 GERRT - round-leaved cranesbill (germanium rotundifolium)
SENVU - common groundsel (Senecio vulgaris)
MALSS - Mallow (Malva L.)
POROL - common purslane (Portulaca oleracea)
grams ai/ha - grams of active ingredient per hectare
Obs - percent control observed
Expected* - percent control expected by Colby equationTable 3. Synergistic weed control following an application of Penoxsulam + Flazasulfuron 83 to 158 days after application - Field trial #3. Penoxsulam Flazasulfuron SOLNI GERRT SENVU POROL (rate in grams ai/ha) Obs Expected* Obs Expected* Obs Expected* Obs Expected* 7 0 70 - 13 - 3 - 0 - 0 25 1 - 23 - 30 - 78 - 7 25 82 70 73 33 73 32 99 78 SOLNI - black nightshade (solanum nigrum)
GERRT - round-leaved cranesbill (Geranium rotundifolium)
SENVU - common groundsel (Senecio vulgaris)
POROL - common purslane (Portulaca oleracea)
grams ai/ha - grams of active ingredient per hectare
Obs - percent control observed
Expected* - percent control expected by Colby equation
Claims (12)
- A synergistic herbicidal mixture comprising an herbicidally effective amount of (a) penoxsulam and (b) flazasulfuron.
- The synergistic herbicidal mixture of Claim 1 in which the weight ratio of flazasulfuron to penoxsulam on an active ingredient (ai) basis is between 1:2.5 and 15:1.
- An herbicidal composition comprising an herbicidally effective amount of the synergistic herbicidal mixture of Claim 1 and an agriculturally acceptable adjuvant or carrier.
- A method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with an herbicidally effective amount of the synergistic herbicidal mixture of Claim 1.
- The method of Claim 4, wherein the undesirable vegetation is controlled in fruit trees, in grapevines, in turf, in sugar cane, in parks and alleyways, in range and pasture, orin industrial vegetation management.
- The method of Claim 5, wherein the fruit frees are selected from pome, stone, tree nut, citrus and olives.
- The method of Claim 4, wherein the synergistic herbicidal mixture of Claim 1 is applied at an application rate of between 14 grams active ingredient per hectare (gai/ha) and 200 gai/ha based on the total amount of active ingredients in the herbicidal mixture.
- The method of Claim 7, wherein the synergistic herbicidal mixture of Claim 1 is applied at an application rate of between 20 grams active ingredient per hectare (gai/ha) and 150 gai/ha based on the total amount of active ingredients in the herbicidal mixture.
- The method of Claim 8, wherein flazasulfuron is applied at a rate between 15 gai/ha and 100 gai/ha, and penoxsulam is applied at a rate between 5 gai/ha and 50 gai/ha.
- The method of Claim 4, wherein the undesirable vegetation is black nightshade, pigeongrass or foxtail millet, common lambsquarter, round-leaved cranesbill, common groundsel, mallow, or common purslane.
- The method of Claim 4, wherein penoxsulam and flazasulfuron are applied either separately or as part of a multipart herbicidal system.
- The synergistic herbicidal mixture of Claim 2, wherein the weight ratio of flazasulfuron to penoxsulam is 3.5:1.
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| PT2531035E (en) | 2010-02-03 | 2014-09-05 | Dow Agrosciences Llc | Synergistic herbicidal composition containing penoxsulam and flazasulfuron |
| AR085074A1 (en) * | 2011-01-20 | 2013-09-11 | Ishihara Sangyo Kaisha | HERBICIDE COMPOSITION |
| AU2012229934B2 (en) * | 2011-03-16 | 2015-07-09 | Corteva Agriscience Llc | Synergistic herbicidal composition containing penoxsulam and pyroxsulam |
| JP5875924B2 (en) * | 2011-04-14 | 2016-03-02 | 石原産業株式会社 | Herbicidal composition |
| US9320274B2 (en) | 2012-09-04 | 2016-04-26 | Dow Agrosciences Llc | Synergistic weed control from applications of aminocyclopyrachlor and clopyralid |
| HK1212860A1 (en) | 2012-09-28 | 2016-06-24 | 美国陶氏益农公司 | Synergistic weed control from applications of aminocyclopyrachlor and triclopyr |
| WO2014052805A1 (en) | 2012-09-28 | 2014-04-03 | Dow Agrosciences Llc | Synergistic weed control from applications of aminocyclopyrachlor and aminopyralid |
| US9149037B2 (en) | 2012-12-12 | 2015-10-06 | Dow Agrosciences Llc | Synergistic weed control from applications of aminocyclopyrachlor and 2,4 dichlorophenoxyacetic acid (2,4-D) |
| US9426991B2 (en) | 2012-12-12 | 2016-08-30 | Dow Agrosciences Llc | Synergistic weed control from applications of aminocyclopyrachlor and picloram |
| CN104994738B (en) | 2012-12-12 | 2019-06-28 | 美国陶氏益农公司 | Synergistic weed control caused by application of penoxsulam and fenfenacet |
| US10412964B2 (en) | 2012-12-14 | 2019-09-17 | Dow Agrosciences Llc | Synergistic weed control from applications of aminopyralid and clopyralid |
| CN104994734B (en) | 2012-12-14 | 2018-06-29 | 美国陶氏益农公司 | Collaboration control of weeds is carried out by application chloroaminopyridine acid and clopyralid |
| ES2693786T3 (en) * | 2013-02-22 | 2018-12-13 | Ishihara Sangyo Kaisha, Ltd. | Use of a herbicidal composition comprising flazasulfuron and mesotrione |
| WO2014130964A1 (en) | 2013-02-25 | 2014-08-28 | Dow Agrosciences Llc | Synergistic weed control with penoxsulam and acetochlor |
| US9717244B2 (en) | 2013-02-25 | 2017-08-01 | Dow Agrosciences Llc | Methods of weed control in pineapple |
| BR112015022099B1 (en) * | 2013-03-15 | 2020-06-16 | Dow Agrosciences Llc | Herbicidal composition, and method for controlling unwanted vegetation |
| WO2014172551A1 (en) | 2013-04-17 | 2014-10-23 | Sepro Corporation | Herbicidal compositions and methods |
| US11026423B2 (en) | 2013-04-17 | 2021-06-08 | Sepro Corporation | Herbicidal compositions and methods |
| WO2015048269A1 (en) * | 2013-09-25 | 2015-04-02 | Dow Agrosciences Llc | Methods of weed control in chicory |
| CN103931634B (en) * | 2014-03-31 | 2016-05-18 | 青岛清原植保服务有限公司 | Containing herbicide and the purposes of penoxsuam |
| CN104396991B (en) * | 2014-11-30 | 2016-05-04 | 南京华洲药业有限公司 | A kind of mixed herbicide containing flazasulfuron, fluroxypyr and trefanocide |
| CN104397000B (en) * | 2014-11-30 | 2016-05-04 | 南京华洲药业有限公司 | A kind of mixed herbicide containing flazasulfuron, fluroxypyr and pyributicarb |
| CN104686556A (en) * | 2015-03-17 | 2015-06-10 | 四川利尔作物科学有限公司 | Weeding composition and application thereof |
| CN105724370A (en) * | 2016-02-04 | 2016-07-06 | 创新美兰(合肥)股份有限公司 | Quinclorac, bispyribac-sodium and penoxsulam compounded dispersible oil suspending agent and preparation method thereof |
| CN106070267A (en) * | 2016-07-13 | 2016-11-09 | 山东奥坤生物科技有限公司 | A kind of Herbicidal combinations containing symetryne and application thereof |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4744814A (en) * | 1984-12-06 | 1988-05-17 | Ishihara Sangyo Kaisha | N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-trifluoromethylpyridine-2-sulfonamide or salts thereof, herbicidal composition containing the same |
| BG60084B2 (en) * | 1990-09-13 | 1993-10-29 | Ishihara Sangyo Kaisha, Ltd. | Herbicide composition |
| WO1998013367A1 (en) * | 1996-09-24 | 1998-04-02 | Dow Agrosciences Llc | N-([1,2,4] triazoloazinyl)benzenesulfonamide and pyridinesulfonamide compounds and their use as herbicides |
| JP4267134B2 (en) * | 1999-07-30 | 2009-05-27 | 石原産業株式会社 | How to control perennial grass weeds in the lawn |
| AU2004218837A1 (en) * | 2003-03-13 | 2004-09-23 | Basf Aktiengesellschaft | Synergistically acting herbicidal mixtures |
| ES2390467T3 (en) * | 2005-02-11 | 2012-11-13 | Dow Agrosciences Llc | Penoxsulam compositions as a herbicide for grass, vineyards and orchards |
| JP5049601B2 (en) * | 2006-03-02 | 2012-10-17 | 石原産業株式会社 | Solid herbicidal composition |
| EP2052606A1 (en) * | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbicide combination |
| JP2009185021A (en) * | 2008-01-10 | 2009-08-20 | Nissan Chem Ind Ltd | Release-controlled particle and solid herbicidal preparation containing the particle |
| CN101310599B (en) * | 2008-05-26 | 2011-11-23 | 北京燕化永乐农药有限公司 | Rice direct seeding field mixed herbicide |
| CN101530105A (en) | 2009-04-21 | 2009-09-16 | 北京颖泰嘉和科技股份有限公司 | Herbicide composition containing sulfonylurea, pyridine and penoxsulam and use thereof |
| CN101601404B (en) * | 2009-07-23 | 2013-12-11 | 江苏辉丰农化股份有限公司 | Weeding composition containing penoxsulam and bensulfuron-methyl |
| PT2531035E (en) | 2010-02-03 | 2014-09-05 | Dow Agrosciences Llc | Synergistic herbicidal composition containing penoxsulam and flazasulfuron |
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- 2012-07-31 IL IL221214A patent/IL221214A/en not_active IP Right Cessation
- 2012-08-02 CO CO12130467A patent/CO6571896A2/en active IP Right Grant
Also Published As
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|---|---|
| BR112012019311B1 (en) | 2018-08-21 |
| CR20120401A (en) | 2012-09-13 |
| JP2013518885A (en) | 2013-05-23 |
| BR112012019311B8 (en) | 2022-10-11 |
| MX2012009045A (en) | 2012-10-01 |
| ES2477515T3 (en) | 2014-07-17 |
| AU2011213127B8 (en) | 2015-06-25 |
| EP2531035A2 (en) | 2012-12-12 |
| KR101829933B1 (en) | 2018-02-19 |
| AU2011213127A8 (en) | 2015-06-25 |
| BR112012019311A2 (en) | 2016-08-02 |
| PT2531035E (en) | 2014-09-05 |
| US20110190136A1 (en) | 2011-08-04 |
| AU2011213127A1 (en) | 2012-08-16 |
| US9179679B2 (en) | 2015-11-10 |
| IL221214A0 (en) | 2012-10-31 |
| CN103037695A (en) | 2013-04-10 |
| AR081622A1 (en) | 2012-10-10 |
| NZ601463A (en) | 2014-08-29 |
| JP5806683B2 (en) | 2015-11-10 |
| WO2011097191A3 (en) | 2012-01-12 |
| PL2531035T3 (en) | 2014-10-31 |
| CN103037695B (en) | 2015-02-04 |
| WO2011097191A2 (en) | 2011-08-11 |
| IL221214A (en) | 2015-04-30 |
| KR20120139725A (en) | 2012-12-27 |
| AU2011213127B2 (en) | 2015-02-26 |
| CO6571896A2 (en) | 2012-11-30 |
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